In honor of Willie Nelson’s Outlaw Festival, coming to Hersheypark Stadium on Sept. 10, WXCY’s Brad Austin and LNP’s Jenelle Janci discuss the life and legacy of Nelson in this month’s Country Confidential.

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Brad Austin: It’s so odd that people like Willie Nelson have become almost counterculture. He was the Luke Bryan of his time, and now, he is revered as an icon, but he’s counterculture. You don’t see his T-shirts every day. His albums aren’t going to be selling a million copies. But, he was that guy, and he made that transition from the “it” guy at the time to icon, and that’s hard to do, because there have been a bunch of other artists that never made that transition.

Brad: That’s fantastic.

Jenelle: So, when I went to a Willie Nelson show in Maryland a couple of weeks ago, I sent a video to him and said, “Don’t cry.”

Brad: It’s funny how Willie is perceived through the generations. You and I, neither of us were born when Willie was the Luke Bryan of country music. We came into it when Willie was considered an old-timer. Really, by ’80-’85, Willie was pretty much done with his mainstream success. Country music, I think different than any other format, has a way of being extremely cyclical. You get a good 10-12 years out of some superstars, and if you’re lucky, if you’re Kenny Chesney, Tim McGraw, you’re on year 20 now. And that’s very rare because there’s very few artists who can reinvent themselves. I think the reason why someone like Willie has gone on into icon status but may not be part of the mainstream as long as he could have is because he was just Willie. And you were going to accept him or not accept him, but he was going to still be Willie.

Jenelle: The other thing about him is that he’s continued to release original music. Artists who are his age and have as much status as he has don’t really need to do that. He could sell concert tickets without making new music. It’s not just throwaway stuff either. That last album he had, “God’s Problem Child,” was pretty high quality.

Brad: I can only speak for country, but there comes a point in every artist’s career — Vince Gill has gone through it, George Strait has gone through it, Toby Keith, in a way, is going through it right now — where you just no longer have hit songs on the radio, whatever the factor may be. You have to make a conscious decision: “Do I want to keep writing and putting out music?” If you look, the ones that continue to do it are the ones that write almost all their music. You’re not going to get pitched the best songs in town if you’re 15 years past your last No. 1 hit.

Jenelle: I’d also argue that something that’s helped people my age to at least know who he is is his advocacy for marijuana legalization. If people can’t name a Willie Nelson song, they at least know him as the guy who really likes pot. Whenever there’s something political that happens with marijuana legalization, I feel like he’s always quoted. Someone always reaches out to him to get his opinion.

Brad: I call him a counterculture icon because marijuana consumption is still counterculture. It’s not mainstream. Anything that’s not mainstream I consider counterculture. But Willie has, in some way, and I don’t think it’s any advocacy of his own, I just think he’s been the most consistent with the message for the longest time. But you’re right — anytime marijuana comes up, Willie Nelson’s name is there. It has become an accepted part of culture that Willie Nelson is a stoner.

Jenelle: So, we mentioned his transition from being the mainstream “it” guy to counterculture. What else, from an industry standpoint, makes his career so notable?

Brad: People who only know him as the grandfatherly, long-braided ponytail, marijuana advocate probably don’t know how Willie started. Willie started as a songwriter, first and foremost, and he used to wear suits. He wrote “Crazy” for Patsy Cline. Then, he made the transition into being a mainstream artist. (As a) mainstream artist, Willie had several very big songs. Then came the mid-to-late ’60s and the early ’70s and outlaw music. I kind of call it country’s answer to Woodstock. There were a group of people who loved country music but felt like they were the outcasts to society like a lot of people from the Woodstock generation felt. I think that’s what bred the outlaw movement of country, which Willie gravitated right into. I think for 40 years, Willie has been one of the most consistent artists in country music.